Monomeric emulsion stabilizers

ABSTRACT

A novel class of monomeric emulsion stabilizers consists of certain types of ethylenically-unsaturated radicals covalently linked to a quaternary nitrogen atom which in turn is covalently linked to a lipophilic radical. Such monomers will polymerize with other ethylenically-unsaturated radicals forming self-stabilized, surfactant-free polymeric dispersions.

This is a division of Ser. No. 496,321, filed Aug. 9. 1974, now U.S.Pat. No. 3,928,423, which is a division of Ser. No. 272,282, filed July17, 1972, now abandoned, said Ser. No. 272,282 being a division of Ser.No. 867,899, filed Oct. 20, 1969, since issued as U.S. Pat. No.3,780,092.

This invention relates to stabilizing agents for emulsionpolymerization. More particularly it relates to a class of quaternizedorganic salts which serve simultaneously as stabilizing agents foremulsion polymerizations and as monomeric reactants in thepolymerization, so that the salts become an integral part of thepolymer, which is thereby self-stabilized without the use ofsurfactants.

Polymeric latices, derived from ethylenically-unsaturated monomers, arewidely used for a variety of applications, such as adhesive masses andbinders for nonwoven fabrics. Most conventional polymeric latices areproduced by an emulsion polymerization process, in which monomericmaterials are polymerized while they are dispersed in an aqueous mediumby means of a surface active agent. The surface active agent may beanionic in nature, such as soap or sodium lauryl sulfate. Alternatively,it may be of nonionic type as represented by various ethylene oxidederivatives, or by polyhydroxy compounds, or it may be cationic, asrepresented by alkyl ammonium halides. Cationic agents are preferablycombined with a nonionic agent for improved performance. Thepolymerization of monomeric materials is also frequently effected in thepresence of water-soluble protective colloids or stabilizing agents. Anyof the above emulsifying or stabilizing agents leads to the presence ofa water-sensitive ingredient in the final polymeric latex. For latexutilizations wherein wet strength and resistance to the influence ofwater are desirable, as in most paper coatings nonwoven fabrics, certainpressure-sensitive adhesive tapes, and the like, the presence of awater-sensitive ingredient in the polymeric mass is undesirable.

A preferred method of avoiding the presence of water-sensitive elementsin a polymeric latex is to employ what is termed herein monomericemulsion stabilizers -- that is, a class of organic monomer whichco-polymerize with the ethylenically-unsaturated monomers, becoming apart of the final polymer, but which stabilize the polymerizationprocess against the formation of coagulum and against subsequent phaseseparation. Such monomeric emulsion stabilizers may becationically-charged nitrogen compounds as set forth in my U.S. Pat. No.3,399,159 wherein the use of monomers such as vinyl pyridines,acid-amines, and certain nitrogen-containing acrylic derivatives isdescribed.

Also, in my copending application Ser. No. 769,355, filed Oct. 21, 1968,there is described a process for preparing monomeric emulsionstabilizers containing a quaternized nitrogen atom ionically linked toan acidic group, such as a sulfate, sulfite, sulfonate, or phosphate,which acid group is covalently bonded to a lipophilic group of 8 to 24carbon atoms.

It is an object of the present invention to prepare a new and usefulclass of monomeric emulsion stabilizers containing a quaternizednitrogen atom covalently linked to an ethylenically-unsaturated radicaland to a lipophilic group, and ionically linked to an anionic group.

It is a further object of the invention to prepare a new and usefulspecies of self-stabilized, surfactant-free polymeric emulsion suitablefor use as coatings, binding agents for nonwoven fabrics, adhesives, andthe like. Other objects of the invention will be apparent from thefollowing specification and claims.

It has now been found that the polymerization ofethylenically-unsaturated monomers may be advantageously carried out ifa major portion of such a monomer or mixture of monomers iscopolymerized with a minor proportion of a quaternized monomer of thegeneral formula: ##STR1## where V is an ethylenically-unsaturatedradical selected from the following three classes:

a. acid ester groups or acid amido groups derived from the dicarboxylicunsaturated acids maleic, fumaric, citraconic, or itaconic, such asHO--CO--CH=CH--COO--, HO--CO--CH=CH--CONH--, HO--CO--CH=C(CH₃)--COO--,HO--CO--CH=C(CH₃)--CONH--, ##STR2##

b. acrylic ester or acrylamido groups represented by the formulas CH₂=CR₄ --COO-- and CH₂ =CR₄ --CONH--, where R₄ is H or CH₃ ;

c. allyl, CH₂ =CH--CH₂ --; methallyl, CH₂ =C(CH₃)--CH₂ --; vinyloxy, CH₂--CH--O--; allyloxy, CH₂ --CH--CH₂ --O--; methallyloxy, CH₂--C(CH₃)--CH₂ --O--; vinyl acetoxy, CH₂ =CH--O--CO--CH₂ --; allylacetoxy; CH₂ =CH--CH₂ --O--CO--CH₂ --; and methallyl acetoxy, CH₂=C(CH₃)--CH₂ --O--CO--CH₂ --.

In the formula given above, the A moiety of the monomeric emulsionstabilizer is zero when V is allyl, methallyl, vinyl acetoxy, allylacetoxy, or methallyl acetoxy. Otherwise, A is a divalent radicalselected from the classes consisting of

a. ethylene, --CH₂ --CH₂ --; propylene, --CH₂ --CH₂ --CH₂ --;hydroxypropylene, --CH₂ --CHOH-CH₂ --; acetoxypropylene, ##STR3## andisopropylene, --CH₂ --CH(CH₃)--, ethylene,

propylene, isopropylene, and hydroxypropylene being preferred;

b. --O--CH₂ --CHR₄ (O--CH₂ --CHR₄)_(n) -- where n equals zero to fourand R₄ again is H or CH₃.

The quaternary nitrogen group -N.^(+R) ₁.R₂.R₃ contains a lipophilicradical R₃. By the term lipophlic radical in the claims andspecification herein is meant a radical containing an aliphatichydrocarbon chain having from about 7 to 28 carbon atoms, with a chainof 9 to 18 carbon atoms preferred. This hydrocarbon group may becovalently linked to the nitrogen either directly or through one of thefollowing intermediate linkages: a benzyl group; an ester group such as--CH₂ --CH₂ --O--CO--R₃ ; a polyalkylene oxide group such as --O--CH₂--CHR₄ --(O--CH₂ --CHR₄)n--OR₃ where R₄ is H or CH₃ and n is 0 to 4; analkyl acetoxy or alkyl acetamido group such as --CH₂ --CO--OR₃ and --CH₂--CO--NHR₃ ; alkyl alkylene ethers such as --CH₂ --O--R₃ ; and alkylamides such as --CH₂ --CH(CH₃)--NH--CO--R₃. The lipophilic radical R₃may be linear or branched, saturated or unsaturated.

In the preferred embodiments of the invention, R₁ is an alkyl or benzylgroup of from 1 to 7 carbon atoms, and R₂ is either an alkyl or benzylgroup of from 1 to 7 carbon atoms or a group selected from the classconsisting of R₅ --O--CO--CH₂ -- and R₅ --NH--CO--CH₂ -- where R₅ is Hor an alkyl group of from 1 to 4 carbon atoms. Cases where R₁ and R₂ arelower alkyl groups, especially methyl groups, are preferred.

R₁ and R₂ may also be valence bonds of a cyclic amine of the piperidineor morpholine type, ##STR4##

In the monomeric emulsion stabilizers of this invention, the X which isionically linked to the quaternary nitrogen is an acid radical selectedfrom the class consisting of F⁻, CI⁻, Br⁻, I⁻, CH₃ SO₄ ⁻, C₂ H₅ SO₄ ⁻,and ##STR5## with CI⁻, Br⁻, or CH₃ SO₄ preferred.

Typical reaction procedures for producing the monomeric emulsionstabilizers of this invention include the reaction of an appropriateethylenically-unsaturated alkylene halide with a tertiary aminecontaining a lipophilic group or with an appropriate ring compound inwhich nitrogen is a ring member: or the reaction of a halogenatedcompound containing active halogen with an ethylenically-unsaturatedcompound containing a tertiary amine.

Representative preparations are the reactions between allyl chloride anddimethyl dodecyl amine or dimethyl hexadecyl amine; between allylbromide and N-cocomorpholine, in which the nitrogen atom in themorpholine ring is covalently bonded to a mixture of saturated alkylgroups averaging 12 carbon atoms; between dimethyl allyl amine anddodecyl chloroacetate; and between maleic anhydride and the reactionproduct of dimethylamino ethanol and lauryl bromide. Specificillustrations of these and other reactions will be given below in thefollowing examples, together with illustrations of their use asmonomeric emulsion stabilizers.

EXAMPLE 1.

Preparation and Use of Allyl Dodecyl Dimethyl Ammonium Chloride.

23 grams of dimethyl dodecyl amine were dissolved in 31 grams of H₂ Oand 9 grams of allyl chloride were added. After 6 hours stirring at 25°C some precipitation had occurred. 50 grams more H₂ O were added andstirring was continued for 16 hours, resulting in a slightly cloudyhomogenous solution.

18 grams of this solution were dissolved in 290 grams of H₂ O, and 100grams of ethyl acrylate were emulsified therein by gradual addition withstirring. The pH of the emulsion was about 6.0. It was cooled to 17° Cand 0.3 grams of 3% H₂ O₂ in H₂ O were added, followed by the dropwiseaddition of a reductant solution (0.02 grams of ferrous ammonium sulfateand 0.5 grams of ascorbic acid in 10 grams of H₂ O). A nitrogenatmosphere was maintained throughout the polymerization in all examples,polymerization being initiated in the present instance after 1.8 gramsof reductant solution had been added. The exotherm was 33° C in abouttwo minutes. Addition of 2 grams more reductant and 2 grams more of 3%H₂ O₂ after the reaction had cooled gave a 5° C exotherm. The yield ofpolymer formed was over 90% of theoretical, and no coagulum was formed.

Essentially similar results were obtained when the ethyl acrylate wasreplaced by a mixture of 10 parts of ethyl acrylate and 74 parts of2-ethylhexyl acrylate. The above precedure was also repeated usingdimethyl hexadecyl amine in place of dimethyl dodecyl amine, and using amixture of 20 grams of vinyl acetate and 80 grams of 2-ethylhexylacrylate as the principal monomer.

EXAMPLE 2. Preparation and Use of Vinyloxyethyl DimethylTridecyloxycarbonylmethyl Ammonium Chloride

28.8 grams of dimethylaminoethyl vinyl ether were dissolved in 98 gramsof acrylonitrile. After cooling the solution to 15° C, 69.3 grams oftridecylchloroacetate were added with stirring. Stirring was continuedfor 72 hours at 25° C. Analysis showed 100% conversion to thequaternized ammonium chloride.

6 grams of the above solution were dissolved in 280 grams of H₂ O, towhich was added with stirring a mixture of 80 grams of ethyl acrylate,10 grams of butyl acrylate, and 7 grams of acrylonitrile. The pH of theresulting emulsion was between 5.0 and 5.5. The emulsion was cooled to17° C, after which polymerization was initiated and maintained using H₂O₂ and reductant as in Example 1. There was no coagulum formed in theresulting polymeric emulsion, and the yield was 92% of theoretical.

EXAMPLE 3. Preparation and Use of Methacryloyloxyethyl DimethylDodecyloxycarbonylmethyl Ammonium Chloride.

15.9 grams of dimethylaminoethyl methacrylate and 26.6 grams of dodecylchloroacetate were stirred together in 45 grams of ethyl acetate at roomtemperature. After a short period of stirring, the white crystallinesolid quaternary ammonium compound was formed, and was isolated.

3.0 grams of the above quaternary compound were dissolved in 350 gramsof H₂ O, to which a mixture of 10 grams of ethyl acrylate and 73.6 gramsof 2-ethylhexyl acrylate were added with stirring. The pH of theresulting emulsion was 6.0. It was cooled to 18° C, and polymerizationwas initiated and maintained as in the above examples. The polymer yieldwas about 90%.

If the proper equivalents of dimethylaminoethyl methacrylate andtridecylchloroacetate are used to form the quaternized compound, theresulting methacryloyloxyethyl dimethyl tridecyloxycarbonylmethylammonium chloride acts as a monomeric emulsion stabilizer similar to itsdodecyl homolog.

EXAMPLE 4. Preparation and Use of Allyloxycarbonylmethyl DimethylHexadecyl Ammonium Chloride.

13.5 grams of allyl chloroacetate were added with stirring to 26.9 gramsof dimethyl hexadecyl amine in 40 grams of dimethyl formamide. Twolayers were initially formed, but with continued stirring for 16 hoursat 25° C, a clear, light yellow homogeneous solution was obtained. After6 days standing, the solvent was removed under vacuum at 40° C. Theresultant solid was washed with ethyl ether and dried. The product wassomewhat greasy, and analysis showed 97% of the theoretical chloridecontent present.

Using the same general procedures as in the above examples, a mixture of55 grams of vinyl acetate and 45 grams of butyl acrylate were emulsifiedusing 3% of the weight of the above monomeric emulsifying agent, basedon the weight of vinyl acetate and butyl acrylate, dissolved in 280grams of H₂ O. Polymerization was initiated and maintained as above bythe use of H₂ O₂ and reductant. The yield of polymer was 83%.

EXAMPLE 5.

Preparation and Use of Allyl Dodecylmorpholinium Bromide. 91.3 grams ofN-cocomorpholine and 45 grams of allyl bromide were stirred in 306 gramsof H₂ O at 25° C for 24 hours. The clear, colorless solution contained96% of the theoretical yield of quaternized ammonium salt.

5 grams of the above 30% aqueous solution were dissolved in 1,000 gramsof H₂ O, and a mixture of 160 grams of ethyl acrylate, 20 grams ofacrylonitrile, and 20 grams of butyl acrylate were added with stirring.The resultant emulsion was polymerized by the use of 0.3 grams oft-butyl peroxy maleic acid and 4.1 grams of the ferrous ammoniumsulfate-ascorbic acid reductant solution. The yield of polymer was 96%of theoretical.

EXAMPLE 6. Preparation and Use of 3-(4-Hydroxymaleoyl)-aminopropylDimethyl Tridecyloxycarbonylmethyl Ammonium Chloride

This quaternary compound was prepared in two stages. 20.4 grams ofdimethylamino propylamine were mixed with 55.4 grams of tridecylchloroacetate in 75.8 grams of acrylonitrile. After 72 hours at 25° C,90% of the theoretical chloride content was found in the form of thequaternized salt. The solution was cooled and 19.6 grams of crushedmaleic anhydride were added, cooling being employed to keep theexothermic reaction below 22° C. 100% of the theoretical chloride ionwas found by analysis. 6 grams of the above solution were dissolved in280 grams of H₂ O, and a mixture of 80 grams of ethyl acrylate, 10 gramsof butyl acrylate, and 7 grams of acrylonitrile were added withstirring. The resulting emulsion, pH 4.0 to 4.5, was cooled, andpolymerization was initiated and maintained by the H₂ O₂ -reductantsystem described in Example 1. Less than 1% of coagulum was formed, andthe yield of polymer was 92%.

EXAMPLE 7. Preparation and Use of 2(4-Hydroxymaleoyloxy)ethyl Dimethylp-Dodecylbenzyl Ammonium Chloride

The preparation of this quaternary compound, like that of Example 6, wasa two-stage reaction. 29.5 grams of p-dodecylbenzyl chloride and 8.9grams of dimethylamino ethanol were mixed in 38.4 grams ofacrylonitrile. After 24 hours at 25° C, 9.8 grams of crushed maleicanhydride were added to the clear solution. After 13 days' standing, theseparated crystalline compound was washed with ethyl acetate and dried.

2.25 grams of the quaternary salt were dissolved in 290 grams of H₂ Oand 75 grams of ethyl acrylate were added with stirring. The resultantemulsion was polymerized with the H₂ O₂ -reductant system used inprevious examples. The yield of polymer was 96% of theoretical.

When lauryl bromide was used in the initial quaternization reaction inplace of p-dodecylbenzyl chloride, followed by reaction with maleicanhydride, 2-(4-hydroxymaleoyloxy)ethyl dimethyl dodecyl ammoniumbromide was produced. Its behavior as a monomeric emulsion stabilizer inthe polymerization of ethyl acrylate was essentially similar to thebehavior of 2-(4-hydroxymaleoyloxy)ethyl dimethyl p-dodecylbenzylammonium chloride.

EXAMPLE 8. Preparation and Use of Methacryloyloxyethyl DimethylHexadecyl Ammonium Bromide.

19.3 grams of 2-bromethyl methacrylate and 27.8 grams of dimethylhexadecylamine were mixed at 25° C in 47.1 grams of acrylonitrile. After6 days, 92% of the theoretical bromide was found in the form of thequaternized salt.

3 grams of the above solution diluted to 33% in acrylonitrile were addedto 280 grams of H₂ O. A mixture of 80 grams of ethyl acrylate, 10 gramsof butyl acrylate, and 8 grams of acrylonitrile were added withstirring. Polymerization of the resultant emulsion was initiated andmaintained by the H₂ O₂ - reductant system described in Example 1. Theyield of polymer was 96%.

EXAMPLE 9. Preparation and Use of Allyl DimethylTridecyloxycarbonylmethyl Ammonium Chloride.

8.5 grams of dimethyl allylamine and 27.7 grams of tridecylchloroacetate were mixed together in 36 grams of dimethyl formamide at25° C. After 15 days' standing, petroleum ether was added to precipitateand isolate the crystalline product. Analysis showed that 85% of thetheoretical chloride content was in the form of the quaternized salt.

5 grams of the quaternized compound were dissolved in 290 grams of H₂ O,and 100 grams of ethyl acrylate were added with stirring.

The resulting emulsion was polymerized by the customary H₂ O₂ --reductant system. The yield of usable polymer was over 90%.

When 26.3 grams of dodecyl chloroacetate were substituted for the 27.7grams of the tridecyl chloroacetate, the dodecyl homolog of theabove-described monomeric emulsion stabilizer was prepared. Its functionand behavior are the same as that of the tridecyl compound.

EXAMPLE 10. Preparation and Use of Vinyloxyethyl Dimethylp-Dodecylbenzyl Ammonium Chloride.

11.5 grams of dimethylaminoethyl vinyl ether and 29.5 grams ofp-dodecylbenzyl chloride were stirred together in 41 grams ofacrylonitrile at 25° C for 24 hours. The chloride by analysis was foundto be completely quaternized.

2.5 grams of the above solution were dissolved in 700 grams of H₂ O. Amixture of 200 grams of ethyl acrylate, 25 grams of butyl acrylate, and24 grams of acrylonitrile were added with stirring. The resultantemulsion was polymerized using a total of 35 grams of 3% H₂ O₂ and 11grams of the reductant solution of Example 1. No coagulum was formed,and the polymer yield was 91% of theoretical.

EXAMPLE 11. Preparation and Use of 3-Methacryloyloxy 2-HydroxypropylDimethyl Octadecyl Methyl Ammonium Sulfate.

Equimolar quantities of N-methyl-N-octadecyl amine and glycidylmethacrylate were reacted together in methanol to formmethacryloyloxyhydroxypropyl methyl octadecyl amine. 14.3 grams of theresultant amine were dissolved in 20 grams of dimethyl formamide and 4.2grams of dimethyl sulfate were added slowly with stirring. After 10days' standing at 25° C, 9 grams of crystalline material was isolated,washed with ether, and dried. The sulfate band in the crystallineproduct was identified in the I.R. spectrum.

2.25 grams of the above stabilizer were dissolved in 290 grams of H₂ O.75 grams of ethyl acrylate were added with stirring. Polymerization wasinitiated and maintained by the usual H₂ O₂ -- reductant system. Lessthan 1 gram of coagulum formed, and the polymer yield was 96% oftheoretical.

EXAMPLE 12. Preparation and Use of Allyl Hexadecyl Dimethyl AmmoniumFluoride.

Allyl hexadecyl dimethyl ammonium chloride was prepared by reactingallyl chloride and dimethyl hexadecyl amine as set forth in Example 1.17.8 grams of the chloride in 23.5% aqueous solution were treated with astoichiometric excess of AgF in aqueous solution until analysis of thefiltrate showed only a trace of chloride ion present. Excess silver ionwas removed by the careful addition of NaCl, AgCl being removed byfiltration.

64 grams of ethyl acrylate, 8 grams of butyl acrylate, and 8 grams ofacrylonitrile were emulsified by gradual addition with stirring to 2.4grams (3% by weight) of the allyl hexadecyl dimethyl ammonium fluoridein 120 grams of H₂ O. The pH of the emulsion was about 6.0. It wascooled to 20° C and 10 grams of 3% aqueous H₂ O₂ were added, followed bythe dropwise addition of the reductant solution of Example 1 untilpolymerization was initiated after 5 grams of reductant had been added.The exotherm was 10° C in 13 minutes. A total of 14 grams of reductantand 13 grams of aqueous H₂ O₂ were used to complete the polymerization.No coagulum was formed and the polymer yield was 95%.

EXAMPLE 13. Preparation of Allyl Hexadecyl Dimethyl Ammonium Iodide.

16.8 grams of allyl iodide were dissolved in 44.6 grams of ethyl acetateand 27.8 grams of dimethyl hexadecyl amine were added slowly withstirring at room temperature. Within 15 minutes after the addition ofthe amine was complete, the viscosity of the solution increased andcrystallization occurred. After 24 hours the crystals were filtered,washed with ethyl acetate, and dried. The colorless crystalline productcontained 88% of the theoretical amount of iodide ion.

The proportion by weight of monomeric emulsion stabilizer used tostabilize the polymerization of other ethylenically-unsaturated monomerswill depend on the nature of the latter. In general, 0.1% to 10% ofstabilizer is used, with a preferred range of 1 to 5%. In the case whereethyl acrylate is the major monomer, 0.5% of emulsion stabilizer willgenerally result in a satisfactory polymerization. In the case of2-ethylhexyl acrylate, the amount of stabilizer is increased to from 3to 5%.

Ethylenically-unsaturated monomers suitable for copolymerizing with themonomeric emulsion stabilizers of this invention comprise vinyl acetate,vinyl chloride, acrylonitrile, and acrylic monomers in generalrepresented by the general formula ##STR6## where R₆ is a hydrogen atomor a methyl group, and R₇ is a saturated alkyl radical of 1 to 14 carbonatoms. As is known in the art of preparing acrylic ester polymers, thesoftness of the polymer and the difficulty of initiating polymerizationincrease as the number of carbon atoms in the ester group increases. Inthe practice of this invention, when the acrylic monomer contains morethan 8 carbon atoms in the ester group, it is advantageous to mixtherewith at least about 20% of an acrylic ester with fewer than 4carbon atoms in the ester group to initiate polymerization and enhancethe stability of the dispersion. Therefore, esters in which the estergroup contains from 1 to 4 carbon atoms are preferred.

Mixtures of more than one such ethylenically-unsaturated monomer may beused, and in order to impart special properties of toughness, rigidity,or cross-linking reactivity to the polymer, a minor proportion, usuallyless than 20 mole percent, of the major monomer may be replaced by someother ethylenically-unsaturated monomer such as vinyl esters, typifiedby vinyl laurate and vinyl stearate; vinyl ethers such as vinyl methylether, vinyl ethyl ether, and vinyl butyl ether; di-unsaturated monomerssuch as diethylene glycol diacrylate, ethylene glycol diitaconate,diallyl phthalate, divinyl benzene and the like; acrylic and methacrylicacids, acrylamide and methacrylamide, hydroxyethyl acrylate andmethacrylate, and hydroxypropyl acrylate and methacrylate, and styrene.

Although the above examples using the stabilizers of this inventionrelate to batch processing, their use is equally well adapted tocontinuous polymerization processes.

Having thus described our invention we claim:
 1. Compound correspondingto the formula ##STR7## wherein V is selected from the class consistingof acid ester groups and acid amido groups derived from maleic,(HO--CO--CH=CH--COO--and HO--CO--CH=CH--CONH--), citraconic,(HO--CO--CH=C(CH₃)--COO -- and HO--CO--CH=C(CH₃)CONH--), and itaconicacids (HO--CO-- ##STR8## A is selected from the class consisting ofethylene (--CH₂ --CH₂ --); propylene (--CH₂ --CH₂ --CH₂ --);isopropylene (--CH₂ --CH(CH₃)--); hydroxypropylene (--CH₂ --CHOH-CH₂--); and acetoxypropylene (--CH₂ --CH(OCOCH₃)--CH₂ --) groups;R₁ and R₂are selected from the class consisting of benzyl groups and alkyl groupsof from 1 to 7 carbon atoms; R₃ is a ##STR9## group wherein R is asaturated aliphatic hydrocarbon group of 7 to 28 carbon atoms; and X isa radical selected from the class consisting of F⁻, CI⁻, Br⁻, I⁻, CH₃SO₄ ⁻, C₂ H₅ SO₄ ⁻, and ##STR10##
 2. The compound according to claim 1wherein the compound is 2-(4-hydroxymaleoyloxy) - ethyl dimethylp-dodecylbenzyl ammonium chloride.